Calamity's First Orgy

Introduction: This is the third installment of the Misadventures of Calamity Callahan. Jennifer Callahan is a luscious blond nymphet that stumbles happily into sexual situations. This story takes place after she and her mother's best friend Trish shared a night of passion in Las Vegas. This story takes place before Jen offers herself to John and Steve before her roommate's wedding. Please read the other two stories to get a more complete picture of Jen's character.

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After that night in Las Vegas, I masturbated like a wild woman. My ass fetish was out of control. When I returned home on break, I would go to my room early each evening, and jerk off like crazy. I was now a two hander; a couple of fingers in my snatch with one hand while the other was under me with a finger going in and out of my butt hole. I would dream for hours about the sex message from that little Pilipino girl and the bed I shared with Trish. And Jim, Ohh Jim, jerking off his monster cock, watching us from the closet.

About a month after Vegas, Trish and Jim stopped by, unannounced. They knew I was home on break they had been drinking and were very playful. Trish threw several double entrées my way. Mom and Dad suspected something. They probably guessed it was secret that Trish and I shared about my boyfriend Tom who also made the trip.

I gasped slightly when I first caught Jim's eye.

"Jen, Hun would you mind freshening Jim's drink," Mom asked?

"Huh, ohh sure Mom." I nervously took the drink from Jim's hand. He gave me a knowing alpha male smile. I hope my parents didn't see that or my embarrassment as I turned away from Jim to grab the bourbon. Ohh shit I hope he wasn't admiring my ass.

"You know Bill," Jim said, "I always enjoy Las Vegas. We should plan another trip. The girls love to shop and maybe we can get in a couple of rounds of golf"

"Too busy right now Jim," Dad countered. "Jen has to go back to college and I have several cases hanging over me right now. Maybe after the first of the year."

"Sure Bill," Jim said, "whenever you guys are available let me know?"

"Well, we have to run," Trish announced. "Ohh and I almost forgot why we stopped by. Jen, sweetie, I left a package for you in the car. We need to give you that bracelet you bought in Vegas. It must have become mixed in with our bags. Would you mind running out to the car with us and grabbing it?"

"Sure, just give me a minute to get some shoes. I will meet you outside." I had not bought a bracelet in Las Vegas. Jim and Trish wanted to talk to me away from my parents. I felt a rush thinking of what they were planning next. By now, Trish must have told Jim that I knew he was in the closet watching us and I that I got off on him looking at my naked ass.

They were standing in front of Jim's black Jag when I caught up with them. Trish gently placed her hand on my shoulder "Hun , I know how awkward this must seem for you as it is for us. Your parents have known us for 30 years and never suspected we were swingers. This is something we have respectfully kept from them. Your choices that night were entirely yours and I don't want you to feel any pressure now."

She then handed me a business card, and said, "We have a group. We are always looking for new members. You might be interested in seeing what we do. We are having a costume get together for Halloween. Part of the fun is the anonymity. If you decide to come, I will send you something to wear, book your flights and arrange for a hotel room. Obviously, I would prefer we keep this to ourselves."

I fingered the card while she continued, "First timers come as the wait staff. In that way you can walk around, serve some drinks and enjoy the show. You will get paid very well. You can always use the extra cash for school."

She then reached in her purse and produced a little jewel box. It contained a gorgeous diamond tennis bracelet. Jim and I wanted you to have this." Jim had stood a respectful distance away during the conversation. Trish hugged me and gave me a soft sensual kiss on the cheek.

Jim approached and I thought of Trish and I together on our knees worshipping his cock. He bent down and wrapped one beefy arm around my waist practically lifting me off the ground. He kissed me on the neck. He didn't say a word. Just his alpha smile.

When I was back at school, I couldn't figure out the logistics of a coed going into town to purchase a Big Jim Dildo, so I had to content with my fingers. I called Trish around mid October and started asking questions. She ways coy, but I had enough information to know that I would be attending my first orgy. I was free to watch or participate in any way I wanted. She assured me that I would not be forced into anything that I did not want to do.

"It is important that you try the costume on before you get there," Trish advised. "Well, Jen what is it going to be?"

"Just one more question, You and Jim, how do feel about being with other people? I mean jealously. That night, you would not have minded him taking me?"

"Jen, please don't you feel any guilt. Jim and I are completely open. As you can imagine, he is absolutely wonderful sexually. I would love to share him with you. We have no jealousy. If you want to understand our world, you have to understand that freedom. Please come and enjoy the experience."

Next day, a naughty girl little bow peep costume arrived in the express mail. Inside the note read " Try everything on. You will have to come home a day early for your final fitting and to pick up your staff. Everything else is included."

I took inventory. There were a pair of white pumps with pretty powder blue bows. The heels were at least 5 inches. How would I serve drinks in these without falling over? There were white lace gloves with the fingers cut out with bows. Next were wonderful silky white stockings with delicate matching little blue bows attached at the thigh. The bows clipped into a lacy garter belt attachment . No panties. Hmm.

The white push up bra was equally beautiful. My 36D's cradled comfortably in the silky material. It felt terrific just trying it on. I looked in the mirror at my boobies. I held them up and started fondling, kissing and licking them in the bra. "Jim would you like to put your dick between by tits? Trish would it be ok if your husband put his big fat delicious dick between my tits?" I scooped my tits out and sucked on each nipple while watching myself in the mirror. Oh gawd I hope my roommate is still in the library.

The workmanship on the dress was obvious. Thin lacy material billowed delicately under the skirt. It was high enough so that if I bent slightly my nether regions would be available. I took some time to admire my ass in the mirror. If I was to be exposed like this I wanted the view to be perfect. I decided to be completely shaved, lotioned and slightly perfumed for my debut. A big blue bow was attached to the back of the dress and the front was trimmed in the same powder blue suggesting a layered apron. A blond wig, a beaded white mask and a big white hat with a blue bow finished the ensemble.

I arrived at the designated house for my final fitting. I had changed into my outfit before arriving for a more dramatic entrance. The added height of the heels, and the mask gave me a feeling of power and authority. I walked slowly to the house already loosing myself to the character.

The door of the mansion flew open revealing a swirl of activity like a dress rehearsal for a Broadway play. There was catered food and several seamstresses working on girls in various stages of dress and undress. A flaming gay in a white tuxedo and a white hat not that much different than mine, ushered me to a makeshift fitting room lined with mirrors. The tailor, bald, fat, extremely short, ugly and equally flaming gave me the once over and nodded.....

"Good choice...good choice..." He stood on a carpeted box to adjust my hat and play with the wig. " Wonderful you will make a fine addition to our little cast of characters." He then hopped off the box. One other thing dear would you mind turning around. His face was now ass high and flipped the back of my dress up to check out my ass and pussy. He grabbed my butt with both hands and parted my back end with his little thumbs. " Ohhh wonderful" he said, and actually heard him inhale. The little perv sniffed my ass.

At that point I was ushered into another room where I was given a gold staff and last minute instructions. I would be staying at the best hotel in Hollywood. I was to be picked up 6:00pm and dropped off at 3:00am the next morning. You will be picked up again at 9:00am for your flight back east. The room and any meals or incidentals have been taken care of. I was to be given a base salary of $1,000 cash. I was free to earn any additional tips based on my skills and performance. My combined earnings for the night were to be given to me at 3:00am.

I was then greeted and spot checked by two middle aged women that appeared to be the "producer" and the "director" of the event. They asked me several questions including if I understood what was going to happen here and if I was ready. It was all so professional and organized that I could only imagine how the next night would be.

I was given final node of approval and ushered out. As I left I noticed the detail of the decoration. In the center of the reception hall a large very well detailed fountain in the shape of a giant phallus was being assembled. It had be 15 feet in height with an extremely intricate vein structure. Two workman were screwing the cap or dick head on the shaft. They paused to look at me looking at them. The filthier of the two winked at me. Water would flow from the top of the fountain and be caught in a bowl at the bottom and then recalculated. It was a very impressive center piece.

Two curving staircases up to the second floor would provide the visual framing for the big dick when the guests arrived. Large pillows and staging platforms were being organized in circles around the edges of the room. An open space was kept in the center would be for dancing. Lights and DJ equipment was being set up at the top of the stairs on the second floor landing. There appeared to either a fog machine on the second floor as well.

I went back to the hotel and ordered up some gang bang porn and, of course, masturbated. I then took a long shower, grabbed room service and got some rest. The limo arrived on time and I was taken to the back of the mansion through the servants' entrance.

I changed into my costume and was given a large silver serving tray with condoms, lubricants and various sexual toys. The door would fling open and the sound of sexual excitement and pounding music would explode into kitchen. People were running in and out taking drink; food and whatever else orders. It was organized like a five star restaurant.

One of the cast members, sweet face, thin, dressed like school girl, plaid skirt, argyle socks, starched white blouse, stopped me in the kitchen. "Hey, hey little bow peep...little bow peep.. watch out for that fucking little gnome. I was little bow peep last year. He tried to lock me into a dog cage with him."

She spun around quickly lifted her tray up high in the air and kicked open the kitchen door. I noticed a little candy stripped plug in her butt with a ring attached looking much like a baby's pacifier....humm...interesting people, with shared interests.

I took a deep breath, turned my back to open the door, and pushed through. Even with seeing the prep, I was overwhelmed. At least 150 to 200 very beautiful people: fucking, sucking, jerking off, jerking each other off; laughing, eating; drinking; all in elaborate expenses looking costumes. Girls with incredible bodies glistening and gyrating in the stage light. The platforms were built into large elaborate looking stages some were enormous beds others very detailed looking dungeons or makeshift jail cells still others were designed as showers and bath tubs.

I plunged in. I had to hold my tray above my head in order to work my way through the crowd. With my arms up in the air, the wide skirt of the my costume rode up even higher. Almost immediately I felt some little teeth trying to nip at my ass but in the frenzy off flashing lights and masks and the crush of people there was no way to spot who could have done it.

But I knew it was that little fucking midget tailor. He has to be the gnome. Bastard. He was waiting ambush me when I came out of the kitchen. I was bumped, cupped, groped and pinched several times in the darkness.

I finally caught site of the gnome: white beard; big red hat He disappeared into a dark crowded corner as soon as I spotted him. You little fucking bastard.

Three painted girls ringed the big dick. They were nude and blindfolded. One was painted like some sort of flower with petals painted around her waist. The other two had black and yellow stripes with antenna headdresses suggesting bees. They were chained together by dog collars; ankle and wrist shackles. They had tight little gymnast legs and butts, accentuated by platform heels which allowed them to have their feet above the water level of the fountain's catch basin.

The water, probably mixed with powdered milk, poured from the tip of the big dick. The enslaved gynists danced and writhed suggestively, occasionally allowing the milk water to cascade over their bodies as if they were being drenched in cum. The water was then caught in the basin of the big dick and recirculated to the top.

New entrants to the festivities would stop whisper greetings and fondle the girls like some sort of good luck ritual. I saw Frankenstein tumble backwards into the dick bowl trying to give the flower girl head.

A MILF dressed as a purple witch sucking a pirate's dick caught my attention. She looked at me with his cock in her mouth and smiled as if I were the camera man making a porn movie. As soon as we made eye contact she loving looked back up at the guy she was blowing. I carefully climbed three stairs of a wide platform to get to her and set my tray of various sundries next to her. When I sat beside her she took the cock dripping with saliva and pre-cum, out of her mouth.

She pulled it towards my face. "You want some," she whispered?

"No thank you" I demurely replied. I could not look in the guys face but he did have great looking dick and terrific abs. "What can I get for you," I asked?

She spat on his dick and began messaging the guy's member in a circular motion using both hands. "How would you like to earn 250 bucks? You see that guy over in the corner jerking off?"

I squinted in the light well that was framing the stage and could see the figure of a monk jerking off in the darkness.

"That is my second husband. He stiffed me without a dime in the divorce. He cheated on me and I got nothing. He said I wasn't exciting enough for him. Now he wants me back. He comes to these things to torture himself watching me fucking other guys."

"Ok?"

"He always asked me for anal. He said it would be the ultimate act of intimacy. I never gave it to him. But I am going to let the captain here stick his dick in my ass right now. I want you to oil my bunghole with him watching and then let this guy bone me up the ass."

She went back to sucking the guy's dick. The pirate so enthralled with her technique, I doubt if the guy heard a word of what she was saying.

She raised , licking her way up his abs stopping to suck his nipple and then licking his face. She then turned around and offered her big juicy apple bottom to him and laid her head on a pillow.

She aroused my own anal fetish. I lovingly stroked her hair and then felt the desire to bend down and kiss her on the cheek as she was getting hammered from behind. I kissed and tongued her ear I kissed and caressed her shoulders and back and then worked my way to the source of her pleasure.

She moaned and begged her lover to go faster. She pushed back against him with every stroke. I kissed her ass several times, inches away from the captain's dick. I then went for the lube. I squeezed some right on her bung hole and softly messaged it in. The captain then figured out what the next move and took over messaging his fingers into her ass making her ready for entry .

It gave me a feeling of power being the facilitator of the action. I looked him straight in eye as if I could see behind his makeup. I took his dick out of her pussy and guided it the tip into her ass. I replaced his dick with two fingers in her wet cunt, kissed her ass cheeks again as he gradually penetrated her ass. I was viewing my first anal.

She was making louder noises now, accepting more of her lover inside of her.

I looked up at the Captain and ordered, "You fuck her ass good, you hear me... fuck her ass good." I said it pretty loud and her ex may have heard me over the noise" I then went back to her front end. I seductively licked the fingers that had been in her snatch. I bent over stroked her hair and kissed and licked her face several more times.

"You earned your money baby" she whispered."

The night went on and I scrambled around passing out drinks and toys and twisting the occasional cock. I grew more bold holding my tray even higher displaying my pussy and ass for all who wanted to see.

"Oils, creams, Condoms, dildos, butt plugs, butt plugs anyone, anyone? I was in total control, helping to initiate but being able to slip away without getting into any serious trouble. I loved the feeling of power.

My only problem was that got-damned gnome. I saw him everywhere. He stalked me from a distance waiting for me to let my guard down. Whenever I went from a light well into a darken area I would look down frantically trying to spot and kick the little shit.

I know he got me three more times with nips and bites attacking like an angry little Chihuahua. My heels were so heavy I could not react in time and kick back at him.

I was stopped by a guy dressed like Caesar. He laid on one side watching the girls dance around the big dick while a long haired slave girl lovingly licked is cock and balls. Another girl with large round breasts much bigger mine, bitch, fed him grapes and strawberries one at time. She would put one in her mouth and then bend down to and let him eat it. Or she would cup her breasts with the fruit held in her cleavage. His face would disappear as he burrowed into her breasts.

'Little bow peep" he called while munching contentedly on a strawberry. "Come here dear."

"What can I get for your majesty?"

"His Highness has grown bored with the preliminary festivities tonight and awaits the main event. Tell the director that I would like you to initiate the fertility ritual."

A bit perplexed, I bowed and worked my way quickly back through the crowds to the kitchen and announced that he wanted the fertility ritual.

Several cast members stopped in their tracks. The director scrambled over to me and asked, "He wanted you to initiate the fertility ritual?"

"Y..yes I said hesitantly, exactly what would I have to do?"

The director grabbed my tray and dumped everything off. She then opened a box and produced a huge black and purple dildo which could best be described as a mini- civil war cannon. It was big around as a pop can and had to be at least 10 to 12 inches in length.

"I am not putting that damn thing in me" I screeched in shock.

"You won't have to," she reassured. "Just take it to him, quickly."

I nervously exited the kitchen. The frenetic pace stopped. A spot light hit me as I existed the kitchen and followed me all the way to Caesar. I fell to my knees and crawled over to him and offered the tray up above my head holding it with both hands. My naked ass faced the crowd

He took the dildo off the tray asked me rise and presented to me in a grand gesture. He instructed me to take it over the girl with the flower design around her waist. .